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Unhinged, A Dating Series: It’s Not That Complicated

After a memorable first date, columnist Nicolle Monico shares her thoughts on why simple gestures and thoughtfulness can score you that coveted second date
Khruangbin, san diego
Khruangbin at Rady Shell, 4/16/24

“I got my daughter from a pair of red shoes,” said the woman at the Rady Shell wrapping the VIP bracelets around our wrists. She looked down at my date’s red Vans and continued the story. “I was on my front lawn when a pair of shoes rolled by in the air.”

At the time, the young man had been doing a handstand on his skateboard past her privacy hedge. She could only see his red shoes as he passed by. “The rest is history,” she laughed. 

My date looked at me, and smirked, “This is a good sign.”

I met Caleb (not his real name) through this column. He slid into my DMs after the first post went live, thanking me for understanding what it’s like out there. I hadn’t thought much of it at the time. I had plenty of those types of messages, along with 500 new followers in one day. When I started reaching out to a handful of locals who had messaged me to do some research and interviews, I remembered to go back to his profile.

He was intriguing, listed a bunch of hobbies on his Instagram which was filled with photos of travels. Noticeably absent, however, were pictures of his face. After reaching out for a chat, we scheduled a call a week later to talk about his dating history and the challenges he was facing as a man in his late 30s. For me, this was purely research for my burgeoning column, or so I thought.

There was an ease to our conversation on the phone. Caleb was open and honest, it didn’t feel like he was putting on a show. Still, though, I could hear some inconsistencies in what he was saying and wrote him off as someone who wasn’t ready to date.

Weeks later, I got a text from him asking me out. “Hey would you wanna get a drink sometime?” he wrote. Short and to the point, there had been no messages leading up to this. But Khruangbin, a band whose name I still can’t pronounce, was playing at the Shell and he wanted to take me. I was in. 

A week later, we stood on the grass with VIP bracelets (he wanted me to be able to see, he said) discussing his red shoes. He was cuter than I expected. We talked like old friends, plenty of banter and no uncomfortable moments of silence. With a bottle of red and two wine glasses, we spent the evening chatting, laughing, and flirting.

He was child-like, overly excited to be spending time with me, giddy even. “Your eyes are like a garden,” he said at one point, calling out their hazel coloring. It wasn’t meant to be romantic, I don’t think, he was more blurting out the first thoughts that came to his mind as I took off my sunglasses. But I liked it.

I’m used to fighting for someone’s affection, so feeling wanted is new for me. And Caleb had done his homework, recalling past articles as he asked questions about me. He had clicked on each Unhinged article to learn everything he could.

“Neither,” he had chosen a couple weeks earlier when I had polled readers about which guy I should date between Ryan and Connor. He was paying attention.

Before the headliner, we got another bottle of wine. “The second one has to be more expensive, right? To show your date you’re interested?” he said. Noted. By the end of the evening, I wanted to kiss him. If you’ve been reading this column since the start, you’ll know this isn’t typical for me on first dates. 

A good sign.

As my Uber approached at the end of the night, he asked if he could kiss me. It was simple, sweet. “Send me a text when you get home,” he said as he closed the car door. He asked me out the next morning and we made actual plans. We’ve talked every day since—he gave me his phone’s passcode.

If I’m being honest, I didn’t want to write this post. This is a world of false starts and normally, those conversations exist only between friends and over text. If this goes nowhere, thousands of readers will know. It’ll be embarrassing. But I didn’t start this column to paint an unrealistic picture of dating. There will be lessons learned through Caleb, whether he remains in my life for a week, a season, or more.

Here’s the thing, at the end of the day it’s maybe not that complicated to show someone you’re interested in them. I think Caleb could teach a masterclass on catching a woman’s attention. He made a thoughtful first move. He took me on a cool first date, wasn’t afraid to flirt up a storm, yet remained respectful and didn’t push. He asks questions. He shows actual interest, and doesn’t (yet, at least) leave me guessing if I matter to him. Hell, he even reads my work. So for what it’s worth, hope you’re taking notes, gents.

Oh, and if you’re wondering, he no longer reads the column. “I want you to keep being completely honest with it, that’s what makes it so good…,” he texted. “If you know that I’ll eventually read it, you may alter it in some way that you wouldn’t have previously and I don’t want to do that to you and it.”

For those of you in relationships, I’m curious, what did you do to make your partner fall for you? How did you impress? Did you spring for the expensive bottle, write a love song, or do a handstand on your skateboard? Email us at @[email protected] with your story and a chance to be featured in the Unhinged newsletter.

If you’re new to Unhinged, catch up on all the dating chats you’ve missed here and follow along at @monicles and @sandiegomag on Instagram to know when a new article drops each week.

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By Nicolle Monico

Nicolle Monico is an award-winning writer and the managing digital editor for San Diego Magazine with more than 15 years of experience in media including Outside Run, JustLuxe and The San Francisco Chronicle.

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